A complete study has been made of the reaction of tris(methylthio)methyllithium with aromatic, heteroaromatic, and aliphatic esters. It is a one-pot reaction that despite its complexity, and depending on the reagent ratios, the reaction conditions, and the possible use of additional reagents (N-(methylthio)phthalimide or BuLi), can supply easily, in excellent and reproducible yields, the trimethyl a-keto trithioorthoesters 3 or, alternatively, the dimethyl a-keto dithioacetals 4. The reaction mechanism has been elucidated.
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